(Bis(2-methoxyethyl)amino)sulfur trifluoride → 4-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 2168795Notes

Reaction equation

HRID 2168795 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][N:15]=[N+:16]=[N-:17])[C@H:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCN(S(F)(F)F)CCOC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([CH2:14][N:15]=[N+:16]=[N-:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86657830cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine

Product 1

HCID 866578344-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis (±)-4-azidomethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.95 mmol, 0.5 g) was added bis(2-methoxyethyl)aminosulfur trifluoride (2.34 mmol, 0.52 g) slowly and stirred for 12. The reaction mixture was diluted with DCM (10 mL), washed with aq.NaHCO3 solution, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography using ethyl acetate:hexanes (2:8) to get 4-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester.

Workup

  1. washwashed with aq
  2. dry with materialNaHCO3 solution, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-f2b1e06d38734a9f93f09267f6deaa62
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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